Nifuratel (CAS 4936-47-4) is a racemic nitrofurane derivative with a strong trichomonicidal activity and a broad antibacterial spectrum acting both on Gram-negative and Gram-positive organism. It is also active against Chlamydia trachomatis and Mycoplasma spp. Nifuratel has a very safe toxicological profile being non-toxic in acute tests in mice and rats and it is well tolerated after repeated oral and intravaginal administration. Since no teratogenic effects have been observed nifuratel is indicated also during pregnancy. This compound is currently used for the treatment of vulvo-vaginal infections and eradication of Helicobacter pylori. In contrast with other drugs used to treat the same diseases, no resistance phenomena, in course of nifuratel treatment, have been reported so far.
Nifuratel and the synthesis thereof are disclosed in GB969126. The Chinese patent application CN101037435A discloses the preparation of (S)-Nifuratel starting from enantiopure (S)-epichlorohydrine (CAS 67843-74-7) and using a chemical pathway similar to what already described for the synthesis of racemic Nifuratel. The same Chinese patent application discloses that (S)-Nifuratel has a better anti-inflammatory and anti-fungal activity than the racemic compound; no information is however given about the preparation of (R)-Nifuratel but that it has not been possible to isolate it by resolution of the racemic compound.